Hydrochloric Acid → HCID 66797087, compound

HRID 1487737Notes

Reaction equation

HRID 1487737 reaction equation
[ClH:1].O1CCOCC1.OC(C(F)(F)F)=O.[CH3:15][NH:16][C:17]([C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26]([N:28]2[CH2:33][CH2:32][N:31](C(OC(C)(C)C)=O)[CH2:30][CH:29]2[CH2:41][O:42][C:43]2[CH:44]=[N:45][CH:46]=[CH:47][CH:48]=2)=[O:27])=[CH:21][CH:20]=1)=[O:18]>CO>[ClH:1].[ClH:1].[CH3:15][NH:16][C:17]([C:19]1[CH:20]=[CH:21][C:22]([NH:25][C:26]([N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH:29]2[CH2:41][O:42][C:43]2[CH:44]=[N:45][CH:46]=[CH:47][CH:48]=2)=[O:27])=[CH:23][CH:24]=1)=[O:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 131728854HCID 131728854, compound

Product 1

HCID 66797087HCID 66797087, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4 M HCl in 1,4-dioxane (6 mL, 24 mmol) was added to a solution of tert-butyl 4-(4-(methylcarbamoyl)phenylcarbamoyl)-3-((pyridin-3-yloxy)methyl)piperazine-1-carboxylate TFA salt (103 mg, 0.177 mmol) in MeOH (1 mL). After stirring overnight, the reaction mixture was concentrated under reduced pressure and purified by HPLC (5 to 50% MeCN/0.1% TFA in H2O/0.1% TFA gradient). The fractions containing the desired product were concentrated under reduced pressure. The material was dissolved in MeOH (1 mL) and treated with 4 M HCl in 1,4-dioxane (6 mL). The mixture was concentrated under reduced pressure to give 42.8 mg (55%) of the title compound as a white solid. LC-MS: RT=2.22 min, [M+H]+=370.1.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. custompurified by HPLC (5 to 50% MeCN/0.1% TFA in H2O/0.1% TFA gradient)
  3. additionThe fractions containing the desired product
  4. concentrationwere concentrated under reduced pressure
  5. dissolutionThe material was dissolved in MeOH (1 mL)
  6. additiontreated with 4 M HCl in 1,4-dioxane (6 mL)
  7. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-cc8602430ed545b6a20746d986585ed0
Source dataset
uspto-grants-2016_08
Patent number
US09428522B2

Reaction notes

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